1-Hydroxybenzotriazole → HCID 59331446, compound

HRID 1881925Notes

Reaction equation

HRID 1881925 reaction equation
Cl.[CH3:2][O:3][NH:4][CH3:5].[CH3:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH2:20][CH:21]2[CH2:25][CH2:24][O:23][CH2:22]2)[C:17]([OH:19])=O)=[CH:12][CH:11]=1)(=[O:9])=[O:8].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(#N)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:2][O:3][N:4]([CH3:5])[C:17](=[O:19])[CH:16]([C:13]1[CH:12]=[CH:11][C:10]([S:7]([CH3:6])(=[O:8])=[O:9])=[CH:15][CH:14]=1)[CH2:20][CH:21]1[CH2:25][CH2:24][O:23][CH2:22]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59331529HCID 59331529, compound

Product 1

HCID 59331446HCID 59331446, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-methoxymethanamine hydrochloride (1.22 g) in acetonitrile (40 mL) was added triethylamine (4.35 mL) for neutralization, and 2-[4-(methylsulfonyl)phenyl]-3-(tetrahydrofuran-3-yl)propanoic acid (3.12 g), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (2.40 g) and 1-hydroxybenzotriazole (191 mg) were added under ice-cooling. The reaction mixture was stirred overnight at room temperature, diluted with ethyl acetate, and washed with water and saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (2.96 g, yield 83%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio).

Workup

  1. additionwere added under ice-
  2. temperaturecooling
  3. washwashed with water and saturated aqueous sodium hydrogen carbonate
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a2918f815e444579b16f36e53310b881
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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